A lake surrounded by autumn-colored trees reflecting on the water.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middletown cottages

A rustic cabin with a stone exterior, wooden deck, and a small porch.

1. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$292 nightly
The price is $330
Oct 1 - Oct 2
Total with taxes and fees
Hello Small Stone
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$281 nightly
The price is $293
Oct 1 - Oct 2
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A wooden deck with a barbecue grill and a trash can.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$304 nightly
The price is $344
Oct 1 - Oct 2
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

4. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.6 out of 10, Exceptional, (5 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
$192 nightly
The price is $216
Oct 5 - Oct 6
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A wooden deck with a glass table and chairs, surrounded by lush greenery and trees.

5. Cozy Cottage with Woodstock Scavenger Hunt

Cozy Cottage with Woodstock Scavenger Hunt
Mongaup Valley
10.0 out of 10, Exceptional, (6 reviews)
$247 nightly
The price is $278
Oct 2 - Oct 3
Total with taxes and fees
Cozy Cottage with Woodstock Scavenger Hunt
A house with a view of a bridge and mountains.

6. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (146 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Oct 6 - Oct 7
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

7. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
$237 nightly
The price is $241
Oct 6 - Oct 7
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
An outdoor dining area with tables and chairs, surrounded by greenery and a view of the landscape.

8. Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.0 out of 10, Wonderful, (4 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Oct 5 - Oct 6
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Exterior

9. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$362 nightly
The price is $399
Oct 6 - Oct 7
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
A covered patio with wicker furniture, a fire pit, and a view of a grassy area.

10. Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
$840 nightly
The price is $937
Oct 7 - Oct 8
Total with taxes and fees
Lakefront | Sport Courts | HotTub | GameRoom
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

11. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
$591 nightly
The price is $698
Oct 22 - Oct 23
Total with taxes and fees
Bright Cornwall-on-hudson Vacation Rental!
An outdoor patio with a stone wall, a wooden fence, and a table with chairs.

12. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
$512 nightly
The price is $630
Oct 4 - Oct 5
Total with taxes and fees
Updated Home w/ Patio Half Mile to West Point
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Helpful"
John 1-night trip
Posted 3 hours ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Middletown

Middletown Cottages information

Number of reviews
234
Accommodation
136 Cottages
Lowest Price
$216
Highest Price
$937

Frequently asked questions

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We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
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What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

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